Phthalimide → 2-[3-(1-Diphenylmethylpiperidine-4-yl)-propyl]-isoindol-1,3-dione

HRID 1280778Notes

Reaction equation

[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16]O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43]1(=[O:53])[NH:47][C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12>C1COCC1>[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][N:47]3[C:43](=[O:53])[C:44]4[C:45](=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:46]3=[O:48])[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 20 °C

Procedure

20.3 g (65.6 mmol) 3-(1-diphenylmethylpiperidin-4-yl)-propan-1-ol, 17.2 g (65.6 mmol) triphenylphosphine and 9.7 g (65.6 mmol) phthalimide are suspended in 220 ml THF and a solution of 10.4 ml (65.6 mmol) azodicarbonic acid diethyl ester in 50 ml THF is added dropwise within one hour under protective atmosphere and light cooling (ca. 15-25° C.). After a further three hours, the solvent is removed under vacuum and the residue is crystallized from 60 ml 1-chlorobutane. Yield: 12.9 g (45%).

Workup

customthe solvent is removed under vacuum
customthe residue is crystallized from 60 ml 1-chlorobutane

Sources & evidence

ORD record: ord-5ba647057ace4609b28ab5e648c87dd3
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451816B1

Reaction notes

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